You own the key… You make the rules, and control his release. If you set a release date for him, occasionally use that release date to make him BEG you you extend his chastity sentence.
He may not want to at first, but smother him with love, and tell him you will make it worth his while. He will be putty and so much more your submissive! This will get easier after time, and makes his release so much more precious!
Cock Cages give me the willies. They are game-changers. There’s no turning back. Getting through the fear is 95 percent of the battle.
Cock cages give quite a different dynamics to a couple. My wife originally wanted nothing to do with it, but slowly she warmed up to the idea and now she loves the control and power she possesses. I learned that my needs were secondary to her wants, desires and plans for the future.